Cannot connect to Plex with Plexamp remotely when Plex server is on VPN

Here’s a weird one. I recently started using a VPN on my Plex server. If I turn off my wifi on my Pixel 3a and try to connect to my Plex server via the Plexamp app it just spins and never loads. BUT if I open the Plex app on my phone that DOES connect. And after that connects I can go back into Plexamp and then I see I am connected there as well and everything works perfectly.

So I can connect to my Plex server behind a VPN via Plexamp but ONLY if I open the Plex app on my phone and let it connect there first. Weird huh? Any ideas?

That is weird. Plexamp does have some limitations around networking the regular Plex app doesn’t (currently, at least). Some tips are here ~ https://support.plex.tv/articles/plexamp-network-connectivity-tips/

I’m not sure what Plex would be doing which would then enable Plexamp to work.

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